Triethylamine → (E)-3-(4-Amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-acrylic acid methyl ester

HRID 2283987Notes

Reaction equation

[NH2:1][C:2]1[C:7](C=O)=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[N:17]([CH3:32])[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=4)[N:20]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.C1(P(=[CH:52][C:53]([O:55][CH3:56])=[O:54])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+].[CH2:59](N(CC)CC)C>CS(C)=O>[CH3:56][O:55][C:53](=[O:54])/[CH:52]=[CH:59]/[C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[N:5][C:6]=1[N:10]1[CH2:11][CH2:12][CH:13]([C:16]2[N:17]([CH3:32])[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:30])([F:29])[F:31])[CH:22]=3)[N:20]=2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 4-amino-6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)pyrimidine-5-carbaldehyde (100 mg; 0.22 mmol; 1.0 eq.) in DMSO (2 mL), methyl (triphenylphosphoranylidene)acetate (82.0 mg; 0.25 mmol; 1.1 eq.), lithium chloride (19.1 mg; 0.45 mmol; 2.0 eq.) and triethylamine (0.04 ml; 0.27 mmol; 1.2 eq.) were added. The resulting suspension was stirred at 60° C. overnight. The crude was purified by pre-HPLC (Waters, basic condition) to afford the title compound in 72% yield. LC-MS: (M+1=505, obsd.=505).

Workup

additionwere added
customThe crude was purified by pre-HPLC (Waters, basic condition)

Sources & evidence

ORD record: ord-a26c66b41c4448bb942881d120757856
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

Loading…